5,6-Diphenyl-1,3,4,7-tetra-<i>p</i>-tolyl-1,3,3a,7a-tetrahydropentaleno[1,2-<i>c</i>]furan

Abstract

The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure of this tricyclic-fused compound was characterized using NMR, mass spectroscopy, and X-ray crystallography. This unique linear tricyclic fused furan framework is reported for the first time.

Keywords

• pentaleno[1,2-c]furan
• tricyclic fused rings
• heterocycle